In the olden days, back when I could keep all my photos on Facebook, photo management was simple. I didn’t have that many to begin with; the ones I did have were grouped around events—birthdays, vacations, etc—and easily organized into albums. I also didn’t care much for privacy, or backups.

Then two things happened: iPhone 4S, and Dora. Every day became a photo-op, with two cameras in our pockets ready to shoot. The DSLR was still there for big trips and Dora’s modeling yet another outrageously expensive dress. This gave us:

  • hundred of new photos and hours of video each month coming from four different sources (our two iPhones, a Nikon DSLR, and friends with their own cameras);
  • no time to sort them;
  • more respect for privacy, but at the same time a need to share baby photos with everyone;
  • panic attacks whenever I thought about having to organize the mess of file names, formats, storage, and backup solutions.

We needed a good method to collect all the photos, organize them for easy access, retrieve them quickly for show-off purposes, and back them up both locally and in the cloud.

Having children usually comes at a point in your life when you care less about money and more about your time—though your progeny will do their best to relinquish you of both. The willpower-depleting effects of a toddler’s tantrum are also well-documented. No surprise then that many of the tools listed below have at some point sponsored a certain Mac-centric podcast that has destroyed many family budgets3. No regrets, though—it all works.

Collecting, with Transporter Sync

For simplicity’s sake, I like systems with multiple inputs to have one central gathering node. Unfortunately, our only desktop computer is a ridiculously noisy four-year-old Windows PC which sits in a usually occupied guest bedroom. The fans that buzz with the sound of a thousand bumblebees instantly disqualify it from a job as a media server, so I had to use my Macbook Pro. Thanks to Transporter Sync, that was easier than I thought possible for an SSD-only machine.

Transporter, similarly to Dropbox, has an iOS app that automatically uploads new photos to a predetermined folder. Unlike Dropbox, there is no monthly subscription—you pay once for the device, and keep using it as long as the hard drive is working. It can also act as a NAS-lite—having access to the folders kept only on the remote hard drive without them occupying the limited space of an SSD, through a Transporter Library folder.

Organizing, with Hazel

A folder full of unsorted cryptically named JPEGs and RAWs is less than useful when your parents want to see all the photos from that trip to Naples back in January.

Enter Hazel, the Swiss army knife of file automation. With the rules I’ve set up, it renames photos based on the date and time taken, tags them according to the device that took them, and moves them to the proper Year/Month subfolder. It does the same with our DSLR’s RAW files, placing them in a separate folder. Since the laptop only has 256 Gb, it moves any files older that three months to Transporter Library, the “special” folder kept only on the external hard drive.

We therefore have the last three months’ worth of photos and videos organized by year and month on the laptop, and our entire collection on the external Transporter hard drive.

Access, with Picturelife

In theory, we could get to all those photos using the Transporter iOS app, but we’re not a masochists. It’s slow, ugly, and not meant for browsing media.

Thank FSM for Picturelife! It sucks up all our new photos and videos from the Transporter—though we’ve excluded RAW files since we do have to pay for all that data2—presents them in a nice web and mobile app interface whenever we want it, and can pass them on to Facebook, Shutterfly, Flickr, or wherever else we choose. It will also, from time to time, send you a “this day in the past” email, with photos taken years ago. When you have as many unprocessed photos as we do, it is a great discovery mechanism.

Did I mention it can send photos to Shutterfly with just a couple of clicks? I still have flashbacks of the last holiday season, progress bar dragging glacially, the upload finishing just in time for me to miss the shipping deadline. Good times.

Backup, with Backblaze and SuperDuper!

Keeping everything on the Transporter and Picturelife as on-site/off-site backups would probably be enough for some. Unfortunately, counting on a VC-backed company that might at any point pull an Everpix to hold all our photos does not seem optimal4.

Which is way Backblaze and SuperDuper! keep copies of all those photos as a part of my general backup system1. If you have a Mac and an extra external hard drive, you should also turn on Time Machine. This way, there are three local copies of all the photos, RAWs, and videos (Transporter, SuperDuper! image, Time Machine), a cloud backup of the same (Backblaze), and an easily-accessible collection of JPGs and videos (Picturelife).

Setting this up is neither cheap nor simple5, but it gives you quick and easy access to all your photos, has several levels of backup, and—most importantly—requires little effort to maintain.


  1. Backblaze will back up the Transporter Library folder, since it doesn’t count as network-attached storage. It doesn’t back up NAS drives. 

  2. We keep RAW files in a separate folder, one that’s not on Picturelife’s monitor list 

  3. Which is why this post has affiliate links. 

  4. That being said, Picturelife is the best of its kind and I strongly recommend it. 

  5. I thought about illustrating it with a diagram of a Rube Goldberg machine.